Indole and Benzimidazole Bichalcophenes: Synthesis, DNA Binding and Antiparasitic Activity

Farahat, Abdelbasset A.; Ismail, Mohamed A.; Kumar, Arvind; Wenzler, Tanja; Brun, Reto; Paul, A.; Boykin, David W.

doi:10.1016/j.ejmech.2017.10.056

Cited by 54 publications

(37 citation statements)

References 24 publications

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“…Synthesis of the bisnitrile compounds (5 a–n) . Sodium metabisulphite (1.14 g, 6 mmol) was added to a solution of the diamine 3 a – k (3 mmol) and the aldehyde 4 a – d (3 mmol) in DMSO (10 mL) and the mixture was heated at 140 °C for 30 min.…”

Section: Methodsmentioning

confidence: 99%

Small Sequence‐Sensitive Compounds for Specific Recognition of the G⋅C Base Pair in DNA Minor Groove

Farahat

Guo

Shoeib

et al. 2020

Chemistry A European J

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A series of small diamidines with thiophene and modified N‐alkylbenzimidazole σ‐hole module represent specific binding to single G⋅C base pair (bp) DNA sequence. The variation of N‐alkyl or aromatic rings were sensitive to microstructures of the DNA minor groove. Thirteen new compounds were synthesized to test their binding affinity and selectivity. The dicyanobenzimidazoles needed to synthesize the target diamidines were made via condensation/cyclization reactions of different aldehydes with different 3‐amino‐4‐(alkyl‐ or phenyl‐amino) benzonitriles. The final diamidines were synthesized using lithium bis‐trimethylsilylamide (LiN[Si(CH3)3]2) or Pinner methods. The newly synthesized compounds showed strong binding and selectivity to AAAGTTT compared to similar sequences AAATTT and AAAGCTTT investigated by several biophysical methods including biosensor‐SPR, fluorescence spectroscopy, DNA thermal melting, ESI‐MS spectrometry, circular dichroism, and molecular dynamics. The binding affinity results determined by fluorescence spectroscopy are in accordance with those obtained by biosensor‐SPR. These small size single G⋅C bp highly specific binders extend the compound database for future biological applications.

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Section: Methodsmentioning

confidence: 99%

Small Sequence‐Sensitive Compounds for Specific Recognition of the G⋅C Base Pair in DNA Minor Groove

Farahat

Guo

Shoeib

et al. 2020

Chemistry A European J

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“…butan-1-amine (6). According to literature method [20], 15.00 g of o-phenylenediamine (138.00 mmol, 1.00 equiv.) in 80 mL of ethanol was added with ammonium chloride (0.74 g, 13.80 mmol, 10 mol%) as catalyst followed by gradual tipping of L-leucine (18.08 g, 138.00 mmol, 1.00 equiv.).…”

Section: Synthesis Procedures Synthesis Of 1-(1h-benzo[d]imidazol-2-ylmentioning

confidence: 99%

“…1. A very recent study showed DNA binding and antiparasitic properties of benzimidazole bichalcophenes [15].…”

Section: ■ Introductionmentioning

confidence: 99%

Facile Synthesis, Characterization and <i>in vitro</i> Antibacterial Efficacy of Functionalized 2-Substituted Benzimidazole Motifs

et al. 2019

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A series of functionalized 2-substituted benzimidazole motifs was designed and successfully synthesized via thermal cyclization of 1,2-diaminobenzene on COOH end of L- leucine to achieve benzimidazole derivatives 6 as the essential precursor. The coupling of the precursor 6 with benzaldehyde derivatives a-h, ketone series i-k, and aryl sulfonyl chlorides l-n led to the formation of the targeted 2-substituted benzimidazole motifs 7a-n in improved yields. The targeted benzimidazole motifs were structurally authenticated through their spectral data and microanalytical parameters. The targeted final moieties were investigated for potential antimicrobial activity using the agar diffusion method with gentamicin as the clinical standard. All the compounds had a broad spectrum of activity with compound 7k having the highest remarkable activity with MIC of 0.98 ± 0.02 µg/mL and MBC value of 3.91 ± 0.10 µg/mL. These findings suggest that compound 7k containing camphor might be a good candidate for the design of new antimicrobial small-molecule drugs.

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“…have created indispensable examples for development of new therapeutic agents . A great number of 2‐substituted benzimidazoles have been synthesized and their biological activities reported (Figure ) . A number of these studies has also focused on symmetrical and unsymmetrically substituted bis‐benzimidazoles .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Antiproliferative Activity Studies of Novel Benzimidazole‐Imidazopyridine Hybrids as DNA Groove Binders

et al. 2020

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A novel benzimidazole‐imidazo[1,2‐a]pyridine hybrid; 2‐(imidazo[1,2‐a]pyridine‐8‐yl)benzimidazole and its symmetrical bis‐ derivative 2,2′‐bis‐(imidazo[1,2‐a]pyridine‐8‐yl)‐1H,1H′‐[5,5′]‐bisbenzimidazole were synthesized and characterized. It was found that these two compounds have a strong DNA groove binding and peroxide mediated DNA‐cleavage properties. Furthermore, these molecules were screened against three different human cell lines namely HepG2, DLD‐1 and MDA‐MB‐231, and these compounds were found to have high cytotoxic activities.

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Indole and Benzimidazole Bichalcophenes: Synthesis, DNA Binding and Antiparasitic Activity

Cited by 54 publications

References 24 publications

Small Sequence‐Sensitive Compounds for Specific Recognition of the G⋅C Base Pair in DNA Minor Groove

Small Sequence‐Sensitive Compounds for Specific Recognition of the G⋅C Base Pair in DNA Minor Groove

Facile Synthesis, Characterization and <i>in vitro</i> Antibacterial Efficacy of Functionalized 2-Substituted Benzimidazole Motifs

Synthesis, Characterization, and Antiproliferative Activity Studies of Novel Benzimidazole‐Imidazopyridine Hybrids as DNA Groove Binders

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